US4954161A - Herbicidal composition and method for safening gramineous crops against heterocyclic phenyl ethers - Google Patents

Herbicidal composition and method for safening gramineous crops against heterocyclic phenyl ethers Download PDF

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Publication number
US4954161A
US4954161A US07/294,855 US29485589A US4954161A US 4954161 A US4954161 A US 4954161A US 29485589 A US29485589 A US 29485589A US 4954161 A US4954161 A US 4954161A
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United States
Prior art keywords
difenzoquat
fenoxaprop ethyl
barley
crop
ethyl
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Expired - Fee Related
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US07/294,855
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Ronald S. Pidskalny
Paul G. Kneeshaw
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BASF SE
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American Cyanamid Co
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Assigned to AMERICAN CYANAMID COMPANY reassignment AMERICAN CYANAMID COMPANY ASSIGNMENT OF ASSIGNORS INTEREST. Assignors: KNEESHAW, PAUL G.
Assigned to AMERICAN CYANAMID COMPANY reassignment AMERICAN CYANAMID COMPANY ASSIGNMENT OF ASSIGNORS INTEREST. Assignors: PIDSKALNY, RONALD S.
Priority to PT92790A priority patent/PT92790A/en
Priority to CA002007227A priority patent/CA2007227A1/en
Priority to AU47785/90A priority patent/AU615604B2/en
Priority to EP90100375A priority patent/EP0417379A1/en
Publication of US4954161A publication Critical patent/US4954161A/en
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Assigned to BASF AKTIENGESELLSCHAFT reassignment BASF AKTIENGESELLSCHAFT ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: AMERICAN CYANAMID COMPANY
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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/32—Ingredients for reducing the noxious effect of the active substances to organisms other than pests, e.g. toxicity reducing compositions, self-destructing compositions
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles

Definitions

  • Z is CH 2 OH or COOR 1 ;
  • R 1 is H, C 1 -C 6 alkyl (optionally substituted with one or two halogen atoms and/or by OH), or phenyl (optionally sub- with one or two halogen and/or methyl groups).
  • Fenoxaprop ethyl a herbicide marketed by Hoechst under the trademark EXCEL, is an especially preferred heterocyclic phenyl ether of the present invention. Fenoxaprop ethyl is used in some gramineous crops, but cannot be used in barley because at herbicidally active rates fenoxaprop ethyl is phytotoxic to the barley crop.
  • the combination of a difenzoquat salt and a heterocyclic phenyl ether provides an unexpected benefit.
  • the combination is safe in gramineous crops, including barley.
  • the two herbicides are combined at rates of active ingredient which give control of the undesirable plant species, while sparing the crop from damage. Typical rates of application are about 0.500 kg/ha to 1.00 kg/ha of difenzoquat and about 0.050 kg/ha to 0.220 kg/ha of heterocyclic phenyl ether.
  • the present invention is prepared by tank mixing the two herbicides prior to delivering the herbicidal combination. This method of preparation is advantageous for immediate application to the field.
  • the treated plots are examined at intervals during the growing season and rated for percent control of wild oats and crop injury.
  • the data listed is an average of the replicates for that treatment.

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  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Dentistry (AREA)
  • Plant Pathology (AREA)
  • Engineering & Computer Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Toxicology (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

A herbicidal composition of difenzoquat and a heterocyclic phenyl ether is safe for gramineous crops and effective in controlling grassweeds including wildoats and greenfoxtail.

Description

BACKGROUND OF THE INVENTION
Wild oats and greenfoxtail are among the most troublesome weeds for farmers growing gramineous crops, such as wheat, barley, rye, triticale and other cereal crops. Full season competition can reduce crop yield significantly, resulting in serious economic losses in crop production. One of the most common practices for controlling wild oats and greenfoxtail is the use of postemergent selective herbicides. For example certain heterocyclic phenyl ethers are known herbicides which are effective against certain annual and perennial grass weeds. Unfortunately, these herbicides cannot be used in all gramineous crops, especially barley, because the herbicide injures the crop as well as controlling the weeds.
Therefore what is needed in the art is a herbicide which is effective against grass weeds, including wild oats and greenfoxtail, while protecting the gramineous crop from injury.
SUMMARY OF THE INVENTION
A method for protecting a gramineous crop from injury by a heterocyclic phenyl ether herbicidal compound of formula (I) ##STR1## wherein Y is hydrogen, halogen, CF3, NO2, CN, alkyl, alkoxy or alkylthio,
A is O, S, NH, or N-alkyl,
R is hydrogen or alkyl and
Z is a carboxylic acid, carboxylic ester, carbonamide, carbohydrazide, thioamide, nitrile, hydroxymethyl, acyloxymethyl, carbamoylmethyl, or sulfonyloxymethyl group.
by applying a difenzoquat salt to the heterocyclic phenyl ether in an non-phytotoxic antidotal amount.
Surprisingly, it has been found that the combination of difenzoquat and heterocyclic phenyl ethers controls undesirable plant species, such as wildoats and greenfoxtail, while protecting the gramineous crops from injury.
DETAILED DESCRIPTION OF THE INVENTION
Difenzoquat (or 1,2-dimethyl-3,5-diphenyl pyrazolium) is a known herbicide which selectively controls wildoats in gramineous crops. While other salts of difenzoquat may be employed, the methyl sulfate salt is preferred. Difenzoquat is not used to control greenfoxtail.
Heterocyclic phenyl ethers of formula (I) ##STR2## wherein Y is hydrogen, halogen, CF3, NO2, CN, alkyl, alkoxy or alkylthio,
A is O, S, NH, or N-alkyl,
R is hydrogen or alkyl and
Z is a carboxylic acid, carboxylic ester, carbonamide, carbohydrazide, thioamide, nitrile, hydroxymethyl, acyloxymethyl, carbamoylmethyl, or sulfonyloxymethyl group
are known herbicides which are used in some gramineous crops, but are not used in all such crops because of their phytotoxicity.
Preferred heterocyclic phenyl ethers useful in the present invention include compounds of formula (I) ##STR3## wherein Y is halogen, CF3, NO2, CH3, or methoxy;
A is O, S, or N--CH3 ;
R is H or CH3 ;
Z is CH2 OH or COOR1 ; and
R1 is H, C1 -C6 alkyl (optionally substituted with one or two halogen atoms and/or by OH), or phenyl (optionally sub- with one or two halogen and/or methyl groups).
Halogen preferably stands for fluorine, chlorine or bromine.
Fenoxaprop ethyl, a herbicide marketed by Hoechst under the trademark EXCEL, is an especially preferred heterocyclic phenyl ether of the present invention. Fenoxaprop ethyl is used in some gramineous crops, but cannot be used in barley because at herbicidally active rates fenoxaprop ethyl is phytotoxic to the barley crop.
The combination of a difenzoquat salt and a heterocyclic phenyl ether provides an unexpected benefit. The combination is safe in gramineous crops, including barley. The two herbicides are combined at rates of active ingredient which give control of the undesirable plant species, while sparing the crop from damage. Typical rates of application are about 0.500 kg/ha to 1.00 kg/ha of difenzoquat and about 0.050 kg/ha to 0.220 kg/ha of heterocyclic phenyl ether. In a preferred embodiment of this present invention, the herbicidal combination is applied so as to provide about 0.700 to 0.850 kg/ha of difenzoquat methyl sulfate and about 0.060 kg/ha to 0.100 kg/ha of fenoxaprop ethyl.
The present invention is prepared by tank mixing the two herbicides prior to delivering the herbicidal combination. This method of preparation is advantageous for immediate application to the field.
The present invention may also be prepared as a coformulation or package mix. A variety of commonly employed adjuvants may be added to the active ingredients of the herbicidal combination such as wetting/dispersion agents, surfactants, antifreezing agents and/or antifoaming agents.
The invention is further illustrated in the following non-limiting examples.
EXAMPLE 1
Wild oats (Avena sativa) is seeded at 50 kg/ha in a north/south direction in early May.
Harrington 2-row barley is seeded in an east-west direction at 91 kg/ha in mid-May. The row width is 18 cm. The seed is drilled in with an International harvester 2.6 meter drill to a depth of 5 cm.
All trials employ standard accepted weed science procedures. Applications are made with a CO2 -powered sprayer. Test design is a modified randomized complete block design with four replications. All applications are made post emergence to the weeds and crop.
The test solutions are prepared by tank mixing sufficient quantities of aqueous solutions and/or dispersions of the test compounds.
The treated plots are examined at intervals during the growing season and rated for percent control of wild oats and crop injury. The data listed is an average of the replicates for that treatment.
              TABLE 1                                                     
______________________________________                                    
17 days after treatment                                                   
              RATE                                                        
TREATMENT     (kg a.i./ha)                                                
                          CROP.sup.1                                      
                                    W.O..sup.2                            
______________________________________                                    
A. Control                 0         0                                    
B. Difenzoquat                                                            
              0.850        0        71                                    
C. Fenoxaprop ethyl                                                       
              0.060       46        76                                    
D. Fenoxaprop ethyl                                                       
              0.100       76        81                                    
E. Difenzoquat and                                                        
                0.850 and 25        75                                    
Fenoxaprop ethyl                                                          
              0.060                                                       
F. Difenzoquat and                                                        
                0.850 and 34        71                                    
Fenoxaprop ethyl                                                          
              0.100                                                       
______________________________________                                    
 .sup.1 Crop injury in percent                                            
 .sup.2 Wild oat control in percent                                       

              TABLE 2                                                     
______________________________________                                    
34 days after treatment                                                   
              RATE                                                        
TREATMENT     (kg a.i./ha)                                                
                          CROP.sup.1                                      
                                    W.O..sup.2                            
______________________________________                                    
A. Control                 0         0                                    
B. Difenzoquat                                                            
              0.850        0        90                                    
C. Fenoxaprop ethyl                                                       
              0.060       31        73                                    
D. Fenoxaprop ethyl                                                       
              0.100       89        80                                    
E. Difenzoquat and                                                        
                0.850 and 11        90                                    
Fenoxprop ethyl                                                           
              0.060                                                       
F. Difenzoquat and                                                        
                0.850 and 27        90                                    
Fenoxaprop ethyl                                                          
              0.100                                                       
______________________________________                                    
 .sup.1 Crop injury in percent                                            
 .sup.2 Wild oat control in percent                                       

              TABLE 3                                                     
______________________________________                                    
67 days after treatment                                                   
              RATE                                                        
TREATMENT     (kg a.i./ha)                                                
                          CROP.sup.1                                      
                                    W.O..sup.2                            
______________________________________                                    
A. Control                 0         0                                    
B. Difenzoquat                                                            
              0.850        0        99                                    
C. Fenoxaprop ethyl                                                       
              0.060       30        19                                    
D. Fenoxaprop ethyl                                                       
              0.100       94        63                                    
E. Difenzoquat and                                                        
                0.850 and  8        99                                    
Fenoxaprop ethyl                                                          
              0.060                                                       
F. Difenzoquat and                                                        
                0.850 and 15        97                                    
Fenoxaprop ethyl                                                          
              0.100                                                       
______________________________________                                    
 .sup.1 Crop injury in percent                                            
 .sup.2 Wild oat control in percent
EXAMPLE 2
Following essentially the same procedure as in EXAMPLE 1, Katepwa Spring Wheat is planted with greenfoxtail (Setaria viridis) weeds. The results listed in TABLE 4 show that the combination of difenzoquat and fenoxaprop ethyl is very effective against greenfoxtail and is safe for the wheat crop.
              TABLE 4                                                     
______________________________________                                    
34 days after treatment                                                   
              RATE                                                        
TREATMENT     (kg a.i./ha)                                                
                          CROP.sup.1                                      
                                    G.F..sup.2                            
______________________________________                                    
A. Control                0          0                                    
B. Difenzoquat                                                            
              0.700       0          0                                    
C. Fenoxaprop ethyl                                                       
              0.060       0         85                                    
D. Fenoxaprop ethyl                                                       
              0.100       0         95                                    
E. Difenzoquat and                                                        
                0.700 and 0         95                                    
Fenoxaprop ethyl                                                          
              0.060                                                       
F. Difenzoquat and                                                        
                0.700 and 0         94                                    
Fenoxaprop ethyl                                                          
              0.100                                                       
______________________________________                                    
 .sup.1 Crop injury in percent                                            
 .sup.2 Greenfoxtail control in percent

Claims (7)

What is claimed is:
1. A herbicidal composition for controlling undesirable plant species, selected from the group consisting of wild oats, green foxtail and combinations thereof which are growing in barley comprising a fenoxaprop ethyl in combination with a difenzoquat salt wherein said composition protects said crop from injury.
2. The composition according to claim 1 wherein the difenzoquat is difenzoquat methyl sulfate.
3. A method for controlling undesirable plant species, selected from the group consisting of wild oats, green foxtail and combinations thereof which are growing in the presence of barley, which comprises applying to the locus in which said barley is growing a herbicidally effective amount of fenoxaprop ethyl and a difenzoquat salt, wherein the herbicidal combination is safe for said barley.
4. A method for protecting barley from injury by fenoxaprop ethyl which comprises applying a difenzoquat salt with the fenoxaprop ethyl in a non-phytotoxic antidotal amount.
5. The method according to claim 4 wherein the fenoxaprop ethyl is applied post-emergence.
6. The method according to claim 5 wherein the difenzoquat salt is difenzoquat methyl sulfate.
7. The method according to claim 6 wherein the difenzoquat methyl sulfate is applied at a rate of about 0.700 kg/ha to 0.850 kg/ha and the fenoxaprop ethyl is applied at a rate of about 0.060 kg/ha to 0.100 kg/ha.
US07/294,855 1989-01-09 1989-01-09 Herbicidal composition and method for safening gramineous crops against heterocyclic phenyl ethers Expired - Fee Related US4954161A (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
US07/294,855 US4954161A (en) 1989-01-09 1989-01-09 Herbicidal composition and method for safening gramineous crops against heterocyclic phenyl ethers
PT92790A PT92790A (en) 1989-01-09 1990-01-05 Process for the preparation of a herbicide composition and method for the protection of grapefruit crops against heterocyclic phenolic ethers using a salt of DIFENZOQUAT
CA002007227A CA2007227A1 (en) 1989-01-09 1990-01-05 Herbicidal composition and method for safening gramineous crops against heterocyclic phenyl ethers
AU47785/90A AU615604B2 (en) 1989-01-09 1990-01-08 A herbicidal composition and method for safening gramineous crops against heterocyclic phenyl ethers
EP90100375A EP0417379A1 (en) 1989-01-09 1990-01-09 A herbicidal composition and method for safening gramineous crops against heterocyclic phenyl ethers

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3882142A (en) * 1972-07-13 1975-05-06 American Cyanamid Co 1,2-Dialkyl-3,5-diphenyl pyrazolium salts
US3922161A (en) * 1972-11-17 1975-11-25 American Cyanamid Co Novel herbicidal compositions
US4130413A (en) * 1976-09-10 1978-12-19 Hoechst Aktiengesellschaft Heterocyclic phenyl ethers and herbicides containing same
US4170464A (en) * 1974-10-25 1979-10-09 American Cyanamid Company Herbicidal combinations

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GR67685B (en) * 1979-04-09 1981-09-04 Hoechst Ag
DE3136913A1 (en) * 1981-09-17 1983-04-21 Hoechst Ag, 6230 Frankfurt "HERBICIDAL AGENTS"

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3882142A (en) * 1972-07-13 1975-05-06 American Cyanamid Co 1,2-Dialkyl-3,5-diphenyl pyrazolium salts
US3922161A (en) * 1972-11-17 1975-11-25 American Cyanamid Co Novel herbicidal compositions
US4170464A (en) * 1974-10-25 1979-10-09 American Cyanamid Company Herbicidal combinations
US4130413A (en) * 1976-09-10 1978-12-19 Hoechst Aktiengesellschaft Heterocyclic phenyl ethers and herbicides containing same

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AU4778590A (en) 1990-07-12
CA2007227A1 (en) 1990-07-09
PT92790A (en) 1990-07-31
AU615604B2 (en) 1991-10-03
EP0417379A1 (en) 1991-03-20

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